In the 1800s, travelers along the perilous forest trail known as the Natchez Trace called it the "Devil's Backbone"

Midnight on the Mississippi. In the antebellum city of Natchez, high on a bluff overlooking the river, lights are winking off in the Victorian mansions and plantation homes emblematic of the Old South. But down here on the riverbank, inside the Under-the-Hill Saloon, André Farish (the proprietor here until his son, André Jr., recently took over) has all night to recount some of the legends surrounding the history of Natchez. "U.S. Grant may have slept up at Rosalie Plantation, but he spent his evenings down here," Farish says, as more customers fresh off the paddle-wheeler Delta Queen push through the door. "He had one of the biggest [benders] of the war here trying to figure what to do about Vicksburg. Nobody much cared Grant was a Yankee. Natchez thought the war was bad for business."

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Two centuries ago, the Mississippi city became a destination for keelboats and barges carrying commodities and manufactured goods down the river. After delivering their products and selling the barges for lumber, the boatmen, known as Kaintucks, needed a place to unwind before starting the long walk home to their Kentucky and Tennessee river valleys. They then headed north on a new route conceived and ordered built by President Thomas Jefferson, the Natchez Trace. (A trace was a forest path.) On it, Kaintucks could walk the 450 miles from Natchez to Nashville in three to four weeks. Post riders could carry mail between the two cities in about two weeks.

Today it is possible to cover the same distance in ten hours or less on the Natchez Trace Parkway, a scenic two-lane highway that parallels the Old Trace. Maintained by the National Park Service (NPS), the 444-mile road angles diagonally across Mississippi and cuts through northwestern Alabama before cresting the Tennessee Valley Divide and dropping into Nashville's Cumberland Valley. The parkway is at its most beautiful in spring and fall, when cyclists pedal beneath massive oak canopies dripping with Spanish moss and hikers follow nearby trails bordered by clover, black-eyed Susan and purple chicory. But it's beyond the parkway that the region's history truly comes alive.

With more than 600 antebellum structures, narrow streets originally designed for carriages and several districts listed on the National Register of Historic Places, Natchez, at the southern end of the parkway, boasts dozens of mansions—Magnolia Hall and Rosalie, Longwood and Auburn. They are massive showplaces, built in the early 1800s as grandiose displays of wealth by new millionaires enriched by the invention of the cotton gin.

Natchez just might be the last city in America where it's possible to purchase a piece of 19th-century America at a reasonable price. Several old houses are always up for sale, thanks in part to the Historic Natchez Foundation, a non- profit organization that buys and renovates distressed properties for eventual resale. "We're the humane society for old buildings," says Ronald Miller, an architectural historian who is the foundation's executive director.

In 1800, Natchez—founded by the French in 1716 and later populated largely by Tory refugees fleeing the Revolutionary War—stood at the edge of America's vast frontier. After the Louisiana Purchase of 1803, Jefferson envisioned further westward expansion. He decided, therefore, to bind Mississippi (and the region that would become Alabama) to the rest of the country by broadening the 450-mile forest track called the Natchez Trace.

Even on the newly widened trail, however, the journey was daunting. The route zigzagged through canebrakes, skirted cypress-filled swamps and crossed several large rivers and dozens of smaller creeks before rising 1,000 feet along ridgelines into the Eastern hardwood forest, an expanse of virgin timber so dense that according to local lore, a squirrel could travel from Maine to Texas without touching the ground. Some called the new road the "Devil's Backbone" because of recurring banditry, but the trail's rigors were the greater worry. "I have this day swam my horse five times, bridged one creek, forded several others beside the swamp we had to wade through," the Rev. John Johnson noted in 1812. "At night we had a shower of rain. Took up my usual lodging on the ground in company with several Indians."

By 1810, more than 10,000 Kaintucks rode or hiked northward each year up the Trace. At night they slept in one of perhaps 20 way stations, or rude inns, at stopping points with names like Buzzard Roost and Sheboss Place that advertised "wilderness entertainment" with "great provender and provisions." During the first three decades of the 19th century, the Natchez Trace functioned as the southwest United States' most-traveled road, although it was seldom more than 12 feet wide.

Today, at Milepost 385.9, a broken stone shaft marks the grave of Meriwether Lewis. As a reward for his services, after the epic 8,000-mile exploration of the newly purchased Louisiana Territory with William Clark, Jefferson named Lewis, his former private secretary, governor of the Upper Louisiana Territory, a largely administrative job for which he was ill-suited. His discontent was compounded by his inability to find a wife and finish his written account of the journey. When the War Department demanded additional documentation for some of the expedition's expenses, Lewis decided to go to Washington.

In the late afternoon of October 10, 1809, according to various accounts later offered, Lewis pulled into Grinder's Stand on the Natchez Trace, accompanied by two servants, two heavily loaded packhorses and $100 in cash. "He seemed distraught all evening, pacing back and forth and talking like a lawyer," the innkeeper's wife later recounted. "Sometime after midnight I heard a shot and then Gov. Lewis screamed, ‘Oh Lord.' Then there was another shot."